1,2-bis(2-methoxyphenyl)ethane-1,2-diol | 61080-15-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-bis(2-methoxyphenyl)ethane-1,2-diol
• 英文别名: (1R,2S)-1,2-bis(2-methoxyphenyl)ethane-1,2-diol
• CAS: 61080-15-7
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: WDLYKWVHMWCMCQ-IYBDPMFKSA-N

物化性质

• 沸点：
  463.6±45.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis(2-methoxyphenyl)ethane-1,2-diol 在 4-二甲氨基吡啶 、 对甲苯磺酸一水合物 、 L-Selectride 、 sodium hydride 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 hydroxy(phenyl)acetic acid (1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl ester
  参考文献：
  名称：

  Chiral linker. Part 3: Synthesis and evaluation of aryl substituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for the diastereoselective reduction of α-keto esters

  摘要：

  Five partly novel aryl substituted m-hydrobenzoins were synthesized and the corresponding desymmetrized hydrobenzoin ethers evaluated as open chain chiral auxiliaries in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates, resulting in de values of up to 91%. Two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliary in the same type of reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.017
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 锌 作用下， 以 溶剂黄146 为溶剂， 生成 1,2-bis(2-methoxyphenyl)ethane-1,2-diol
  参考文献：
  名称：

  醇类的光化学反应-II：芳族醇的辐照

  摘要：

  芳香醇的紫外线照射导致形成多种产物：羰基化合物，醚，α-乙二醇和四-芳基-1,4-二恶烷。

  DOI：

  10.1016/0040-4020(82)85088-6

文献信息

• Stereoselectivity in Pinacol-Homocoupling Mediated by Samarium Diiodide
  作者：Peter G�rtner、Max Knollm�ller、Joachim Br�ker

  DOI：10.1007/s00706-003-0061-x

  日期：2003.12.1

   The stereoselectivity of the pinacol-coupling of various substituted benzaldehydes mediated by samarium diiodide was investigated. The dependence of product-ratios, yields, and stereoselectivities on the substrate, the substrate-reagent-ratio, and the solvent is described.

  研究了二碘化sa介导的各种取代苯甲醛频哪醇偶联的立体选择性。描述了产物比，产率和立体选择性对底物，底物试剂比和溶剂的依赖性。
• Pinacolic Coupling of Aromatic Carbonyl Compounds Using Zn Powder in Aqueous Basic Media without Organic Solvents
  作者：Takehito Tsukinoki、Takatoshi Kawaji、Iwao Hashimoto、Shuntaro Mataka、Masashi Tashiro

  DOI：10.1246/cl.1997.235

  日期：1997.3

  Treatment of aromatic carbonyl compounds with Zn powder in 10% aq NaOH solution without using any organic solvents under the mild conditions afforded the corresponding 1,2-diols in good yields.

  在温和条件下，在不使用任何有机溶剂的情况下，用 Zn 粉末在 10% NaOH 水溶液中处理芳香族羰基化合物，以良好的收率得到相应的 1,2-二醇。
• A Samarium “Soluble” Anode: A New Source of SmI2 Reagent for Electrosynthetic Application
  作者：Kamar Sahloul、Linhao Sun、Alexandre Requet、Youhana Chahine、Mohamed Mellah

  DOI：10.1002/chem.201201390

  日期：2012.9.3

  An electrochemical method to prepare solutions of samarium diiodide in THF is reported. The simple electrolysis of a samarium rod provides a rapid and straightforward in situ synthesis of SmI2. The electrogenerated complex catalyzes various CC bond formations. The reagent is produced continuously (see scheme) and leads to efficient organic electrosynthesis with significantly smaller amounts of solvent

  据报道，电化学方法制备了二碘化sa在THF中的溶液。rod棒的简单电解提供了SmI 2的快速，直接的原位合成。电生成的配合物催化各种CC键的形成。试剂是连续生产的（请参见方案），并且可以用比通常所需的溶剂少得多的溶剂进行有效的有机电合成。
• Reductive Coupling of Carbonyl Compounds to Pinacols with Zinc in THF-Saturated Aqueous Ammonium Chloride
  作者：Rahim Hekmatshoar、Issa Yavari、Yahya S. Beheshtiha、Majid M. Heravi

  DOI：10.1007/s007060170083

  日期：2001.6

   In the presence of metallic zinc, aldehydes and ketones experience reductive coupling in tetrahydrofuran-saturated aqueous ammonium chloride (5:3) to afford the corresponding pinacols in moderate to high yields.

  在金属锌的存在下，醛和酮在四氢呋喃饱和氯化铵水溶液（5：3）中经历还原偶联，从而以中等至高收率得到相应的频哪醇。
• MeOH or H 2 O as efficient additive to switch the reactivity of allylSmBr towards carbonyl compounds
  作者：Jianyong Li、Qingsheng Niu、Shanchan Li、Yuehao Sun、Qian Zhou、Xin Lv、Xiaoxia Wang

  DOI：10.1016/j.tetlet.2017.01.091

  日期：2017.3

  aryl ketones mediated by Sm/alkyl halide/MeOH. The results demonstrate that the real reducing species in Sm/alkyl halide/MeOH system should be allylSmBr, and MeOH has elegantly switched the reactivity of allylSmBr from being nucleophilic to being good reductive coupling reagent. Besides, H2O was also found to be a useful additive to realize the pinacol coupling of aliphatic aldehydes and ketones promoted

  烯丙基SmBr（allylSmBr）用MeOH作为助溶剂处理了各种羰基化合物，以进一步了解以前报道的Sm /烷基卤化物/ MeOH介导的芳基酮的还原偶联。结果表明，Sm /卤代烷/ MeOH体系中真正的还原物种应为烯丙基SmBr，并且MeOH很好地将烯丙基SmBr的反应性从亲核性转变为良好的还原偶联剂。此外，还发现H 2 O是实现烯丙基SmBr促进的脂肪醛和酮的频哪醇偶联的有用添加剂。